Pyridine → 2-(Phenyldiazenyl)succinonitrile

HRID 522154

Reaction equation

HRID 522154 reaction equation
[C:1]([CH:3]([CH2:9][C:10]#[N:11])C(OCC)=O)#[N:2].N1C=CC=CC=1.F[B-](F)(F)F.[C:23]1([N+:29]#[N:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[C:23]1([N:29]=[N:30][CH:3]([CH2:9][C:10]#[N:11])[C:1]#[N:2])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 5284485Benzenediazonium tetrafluoroborateHCID 10725530Ethyl 2,3-Dicyanopropionate

Product 1

HCID 1184560602-(Phenyldiazenyl)succinonitrileYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2,3-dicyanopropanoate (1.58 g, 10.38 mmol) in methanol (52 mL) and pyridine (2.52 mL, 31.14 mmol) was cooled to 10° C. in an ice bath. Benzenediazonium tetrafluoroborate was added portion-wise over 20 minutes at 10° C. and the reaction stirred at room temperature for 18 hours. The reaction was concentrated in vacuo and partitioned between DCM and water. The organic layer was dried over magnesium sulphate and concentrated in vacuo to afford the title compound (2.8 g, 28%). The crude product was taken on directly to the next step.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompartitioned between DCM and water
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e04577d859ea4acab1e0bbddfd132a30
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Linked notes

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